NL2035060B1 - A method of recovering polyurethane polymer from a waste polymer textile material that comprises polyester and polyurethane fibers - Google Patents
A method of recovering polyurethane polymer from a waste polymer textile material that comprises polyester and polyurethane fibers Download PDFInfo
- Publication number
- NL2035060B1 NL2035060B1 NL2035060A NL2035060A NL2035060B1 NL 2035060 B1 NL2035060 B1 NL 2035060B1 NL 2035060 A NL2035060 A NL 2035060A NL 2035060 A NL2035060 A NL 2035060A NL 2035060 B1 NL2035060 B1 NL 2035060B1
- Authority
- NL
- Netherlands
- Prior art keywords
- polyurethane
- solvent
- polyester
- polar aprotic
- polymer
- Prior art date
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- 229920002635 polyurethane Polymers 0.000 title claims abstract description 105
- 239000004814 polyurethane Substances 0.000 title claims abstract description 105
- 229920000642 polymer Polymers 0.000 title claims abstract description 95
- 239000004753 textile Substances 0.000 title claims abstract description 90
- 238000000034 method Methods 0.000 title claims abstract description 89
- 229920000728 polyester Polymers 0.000 title claims abstract description 82
- 239000000463 material Substances 0.000 title claims abstract description 81
- 239000002699 waste material Substances 0.000 title claims abstract description 65
- 229920006306 polyurethane fiber Polymers 0.000 title abstract description 19
- 239000003880 polar aprotic solvent Substances 0.000 claims abstract description 60
- 239000011877 solvent mixture Substances 0.000 claims abstract description 29
- 238000000926 separation method Methods 0.000 claims abstract description 22
- 239000007788 liquid Substances 0.000 claims abstract description 12
- 230000001376 precipitating effect Effects 0.000 claims abstract description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 120
- 239000003054 catalyst Substances 0.000 claims description 69
- 239000002904 solvent Substances 0.000 claims description 62
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 52
- 229920002334 Spandex Polymers 0.000 claims description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 38
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 26
- QPKOBORKPHRBPS-UHFFFAOYSA-N bis(2-hydroxyethyl) terephthalate Chemical compound OCCOC(=O)C1=CC=C(C(=O)OCCO)C=C1 QPKOBORKPHRBPS-UHFFFAOYSA-N 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 26
- 229920000139 polyethylene terephthalate Polymers 0.000 claims description 21
- 239000005020 polyethylene terephthalate Substances 0.000 claims description 21
- 239000000178 monomer Substances 0.000 claims description 20
- 230000001476 alcoholic effect Effects 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- -1 alkylene glycol Chemical compound 0.000 claims description 17
- 229920000058 polyacrylate Polymers 0.000 claims description 16
- 229920002239 polyacrylonitrile Polymers 0.000 claims description 14
- 239000004952 Polyamide Substances 0.000 claims description 13
- 229920002647 polyamide Polymers 0.000 claims description 13
- 230000008569 process Effects 0.000 claims description 12
- 238000005406 washing Methods 0.000 claims description 10
- 229920005862 polyol Polymers 0.000 claims description 9
- 150000003077 polyols Chemical class 0.000 claims description 9
- 239000006185 dispersion Substances 0.000 claims description 8
- GNFTZDOKVXKIBK-UHFFFAOYSA-N 3-(2-methoxyethoxy)benzohydrazide Chemical compound COCCOC1=CC=CC(C(=O)NN)=C1 GNFTZDOKVXKIBK-UHFFFAOYSA-N 0.000 claims description 6
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 5
- 238000001704 evaporation Methods 0.000 claims description 5
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 5
- 239000002861 polymer material Substances 0.000 claims description 5
- 239000010784 textile waste Substances 0.000 claims description 5
- 239000000975 dye Substances 0.000 claims description 4
- 239000013538 functional additive Substances 0.000 claims description 4
- 239000006249 magnetic particle Substances 0.000 claims description 4
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 claims description 3
- 230000003197 catalytic effect Effects 0.000 claims description 3
- FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 claims description 2
- 229920002396 Polyurea Polymers 0.000 claims description 2
- CAPAZTWTGPAFQE-UHFFFAOYSA-N ethane-1,2-diol Chemical compound OCCO.OCCO CAPAZTWTGPAFQE-UHFFFAOYSA-N 0.000 claims description 2
- NPANDVNCRMZSFT-UHFFFAOYSA-N propane-1,2-diol;propane-1,3-diol Chemical compound CC(O)CO.OCCCO NPANDVNCRMZSFT-UHFFFAOYSA-N 0.000 claims description 2
- 239000002245 particle Substances 0.000 description 52
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- 239000000835 fiber Substances 0.000 description 24
- 239000011541 reaction mixture Substances 0.000 description 21
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 20
- 238000002474 experimental method Methods 0.000 description 19
- 238000000605 extraction Methods 0.000 description 19
- 239000004744 fabric Substances 0.000 description 19
- 238000002203 pretreatment Methods 0.000 description 15
- 230000000052 comparative effect Effects 0.000 description 14
- 238000001556 precipitation Methods 0.000 description 14
- 125000002091 cationic group Chemical group 0.000 description 12
- 239000011572 manganese Substances 0.000 description 12
- 239000003921 oil Substances 0.000 description 11
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 10
- 125000000217 alkyl group Chemical group 0.000 description 10
- 125000005647 linker group Chemical group 0.000 description 10
- 238000010907 mechanical stirring Methods 0.000 description 10
- 125000001424 substituent group Chemical group 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000012452 mother liquor Substances 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- 238000000956 solid--liquid extraction Methods 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 229910052742 iron Inorganic materials 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 8
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 7
- 238000009835 boiling Methods 0.000 description 7
- 125000005842 heteroatom Chemical group 0.000 description 7
- 229910052723 transition metal Inorganic materials 0.000 description 7
- 150000003624 transition metals Chemical class 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 235000013980 iron oxide Nutrition 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 239000002105 nanoparticle Substances 0.000 description 6
- 238000011282 treatment Methods 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 230000003247 decreasing effect Effects 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 230000034659 glycolysis Effects 0.000 description 5
- 150000004820 halides Chemical class 0.000 description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- IQQRAVYLUAZUGX-UHFFFAOYSA-N 1-butyl-3-methylimidazolium Chemical compound CCCCN1C=C[N+](C)=C1 IQQRAVYLUAZUGX-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 239000000010 aprotic solvent Substances 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 238000006555 catalytic reaction Methods 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 4
- 238000011068 loading method Methods 0.000 description 4
- 229910052759 nickel Inorganic materials 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 238000012691 depolymerization reaction Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000002845 discoloration Methods 0.000 description 3
- 239000013013 elastic material Substances 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 3
- 239000002638 heterogeneous catalyst Substances 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 3
- 239000000395 magnesium oxide Substances 0.000 description 3
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 3
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical group [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 229920001778 nylon Polymers 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 229940043375 1,5-pentanediol Drugs 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
- CETWDUZRCINIHU-UHFFFAOYSA-N 2-heptanol Chemical compound CCCCCC(C)O CETWDUZRCINIHU-UHFFFAOYSA-N 0.000 description 2
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- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical compound OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 description 2
- GYSCXPVAKHVAAY-UHFFFAOYSA-N 3-Nonanol Chemical compound CCCCCCC(O)CC GYSCXPVAKHVAAY-UHFFFAOYSA-N 0.000 description 2
- IWTBVKIGCDZRPL-UHFFFAOYSA-N 3-methylpentanol Chemical compound CCC(C)CCO IWTBVKIGCDZRPL-UHFFFAOYSA-N 0.000 description 2
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- BKQICAFAUMRYLZ-UHFFFAOYSA-N 4-methylheptan-3-ol Chemical compound CCCC(C)C(O)CC BKQICAFAUMRYLZ-UHFFFAOYSA-N 0.000 description 2
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- RZKSECIXORKHQS-UHFFFAOYSA-N Heptan-3-ol Chemical compound CCCCC(O)CC RZKSECIXORKHQS-UHFFFAOYSA-N 0.000 description 2
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- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
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- 229910052779 Neodymium Inorganic materials 0.000 description 2
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- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 229920002873 Polyethylenimine Polymers 0.000 description 2
- IXUOEGRSQCCEHB-UHFFFAOYSA-N Propyl-n-amyl-carbinol Natural products CCCCCC(O)CCC IXUOEGRSQCCEHB-UHFFFAOYSA-N 0.000 description 2
- 229910052772 Samarium Inorganic materials 0.000 description 2
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- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- AEIJTFQOBWATKX-UHFFFAOYSA-N octane-1,2-diol Chemical compound CCCCCCC(O)CO AEIJTFQOBWATKX-UHFFFAOYSA-N 0.000 description 1
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 125000001477 organic nitrogen group Chemical group 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical class [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- WCVRQHFDJLLWFE-UHFFFAOYSA-N pentane-1,2-diol Chemical compound CCCC(O)CO WCVRQHFDJLLWFE-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920006111 poly(hexamethylene terephthalamide) Polymers 0.000 description 1
- 229920000747 poly(lactic acid) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 239000004626 polylactic acid Substances 0.000 description 1
- 229920005594 polymer fiber Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920006375 polyphtalamide Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- UIIIBRHUICCMAI-UHFFFAOYSA-N prop-2-ene-1-sulfonic acid Chemical compound OS(=O)(=O)CC=C UIIIBRHUICCMAI-UHFFFAOYSA-N 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- ILVGAIQLOCKNQA-UHFFFAOYSA-N propyl 2-hydroxypropanoate Chemical compound CCCOC(=O)C(C)O ILVGAIQLOCKNQA-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- VSZWPYCFIRKVQL-UHFFFAOYSA-N selanylidenegallium;selenium Chemical compound [Se].[Se]=[Ga].[Se]=[Ga] VSZWPYCFIRKVQL-UHFFFAOYSA-N 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 1
- 125000005624 silicic acid group Chemical group 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- SZHIIIPPJJXYRY-UHFFFAOYSA-M sodium;2-methylprop-2-ene-1-sulfonate Chemical class [Na+].CC(=C)CS([O-])(=O)=O SZHIIIPPJJXYRY-UHFFFAOYSA-M 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000004759 spandex Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- JBQYATWDVHIOAR-UHFFFAOYSA-N tellanylidenegermanium Chemical compound [Te]=[Ge] JBQYATWDVHIOAR-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- XSMIOONHPKRREI-UHFFFAOYSA-N undecane-1,11-diol Chemical compound OCCCCCCCCCCCO XSMIOONHPKRREI-UHFFFAOYSA-N 0.000 description 1
- BUMVVNKGNPPUME-UHFFFAOYSA-N undecane-1,2-diol Chemical compound CCCCCCCCCC(O)CO BUMVVNKGNPPUME-UHFFFAOYSA-N 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J11/00—Recovery or working-up of waste materials
- C08J11/04—Recovery or working-up of waste materials of polymers
- C08J11/06—Recovery or working-up of waste materials of polymers without chemical reactions
- C08J11/08—Recovery or working-up of waste materials of polymers without chemical reactions using selective solvents for polymer components
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D11/00—Solvent extraction
- B01D11/02—Solvent extraction of solids
- B01D11/0288—Applications, solvents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J11/00—Recovery or working-up of waste materials
- C08J11/04—Recovery or working-up of waste materials of polymers
- C08J11/10—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation
- C08J11/18—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with organic material
- C08J11/22—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with organic material by treatment with organic oxygen-containing compounds
- C08J11/24—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with organic material by treatment with organic oxygen-containing compounds containing hydroxyl groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2367/00—Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
- C08J2367/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
- C08J2375/04—Polyurethanes
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
- Y02W30/00—Technologies for solid waste management
- Y02W30/50—Reuse, recycling or recovery technologies
- Y02W30/62—Plastics recycling; Rubber recycling
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Sustainable Development (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Separation, Recovery Or Treatment Of Waste Materials Containing Plastics (AREA)
Claims (26)
1. Werkwijze voor het herwinnen van polyurethaanpolymeer uit een afvalpolymeertextielmateriaal dat polyester- en polyurethaanvezels omvat, de werkwijze omvattende de stappen van: a) verschaffen van het afvalpolymeertextielmateriaal in geshredderde of gesneden vorm; b) in contact brengen van het afvalpolymeertextielmateriaal in geshredderde of gesneden vorm met een polair aprotisch oplosmiddel bij een temperatuur van 25 tot 125 °C om het polyurethaan ten minste deels op te lossen in het polaire aprotische oplosmiddel terwijl het polyester in hoofdzaak onbeinvioed blijft: c} scheiden van het polyester van het oplosmiddelmengsel omvattende het polaire aprotische oplosmiddel en het daarin opgeloste polyurethaan door middel van vast-vloeistof scheiding: d) precipiteren van opgelost polyurethaan in het oplosmiddelmengsel: e) scheiden van het geprecipiteerde polyurethaan van het oplosmiddelmengsel om polyurethaanpolymeer en gebruikt polair aprotisch oplosmiddel te verkrijgen; f) optioneel hergebruiken van ten minste een deel van het gebruikte polaire aprotische oplosmiddel in stap b).
2. Werkwijze volgens conclusie 1, waarin precipiteren van opgelost polyurethaan in het oplosmiddelmengsel in stap d) toevoegen van water aan het oplosmiddelmengsel omvat, waarin oplosmiddelmengsel optioneel gekoeld wordt tot een temperatuur onder de contacttemperatuur van stap b) vóór, gedurende of na toevoegen van het water.
3. Werkwijze volgens conclusie 2, waarin het toegevoegde water een temperatuur heeft van 1-100 °C bij omgevingsdruk, met meer voorkeur van 5-50 °C bij omgevingsdruk, met nog meer voorkeur van 10-40 °C, en met de meeste voorkeur van 15-30 °C bij omgevingsdruk
4, Werkwijze volgens één van de voorgaande conclusies, waarin het polyurethaanpolymeer verkregen in stap e) een Mn heeft van ten minste 50000 Da.
5. Werkwijze volgens één van de conclusies 2-4, waarin het toegevoegde water wordt gescheiden van het gebruikte polaire aprotische oplosmiddel verkregen in stap e) vóór het optionele hergebruik van het polaire aprotische oplosmiddel volgens stap f).
6. Werkwijze volgens één van de voorgaande conclusies, waarin het polyester verkregen in stap c) wordt uitgeknepen en/of gewassen om polair aprotisch oplosmiddel dat nog aanwezig is in het polyester verder te verwijderen, waarin het optionele wassen bij voorkeur tegenstrooms uitgevoerd wordt.
7. Werkwijze volgens één van de voorgaande conclusies, verder omvattende de stap van: g) in contact brengen van het polyester verkregen in stap c) met een polyoloplosmiddel bij een temperatuur van 50 tot 200 °C om eventueel achtergebleven polyurethaan verder op te lossen in het polyoloplosmiddel en verdampen van het polaire aprotische oplosmiddel terwijl het polyester in hoofdzaak onbeïnvloed blijft, en hy) scheiden van het polyester van het polyoloplosmiddelmengsel omvattende het polyoloplosmiddel, het eventueel achtergebleven polyurethaan dat daarin is opgelost en eventueel achtergebleven polair aprotisch oplosmiddel, door vast- vloeistof scheiding.
8. Werkwijze volgens conclusie 7, waarin de hoeveelheid van het polaire aprotische oplosmiddel dat nog steeds aanwezig is in het polyester na stap h) relatief ten opzichte van de hoeveelheid alcoholisch oplosmiddel minder dan 1:1 bedraagt.
9. Werkwijze volgens één van de conclusies 7 en 8, waarin het afvalpolymeertextielmateriaal verder polyamidevezels omvat, het polyamide wordt opgelost in stap g) en dan gescheiden van het polyester in stap h).
10. Werkwijze volgens één van de voorgaande conclusies, waarin het afvalpolymeertextielmateriaal verder acrylpolymeervezels omvat. het acrylpolymeer wordt opgelost in stap b) en het opgeloste acrylpolymeer wordt gescheiden van het eerste mengsel in stap d).
11. Werkwijze volgens één van de voorgaande conclusies, waarin het afvalpolymeertextielmateriaal verder functionele additieven bevat zoals kleurstoffen, en de functionele additieven worden opgelost in het polaire aprotische oplosmiddel en gescheiden van het polyester in stap d) met het polaire aprotische oplosmiddel.
12. Werkwijze volgens één van de voorgaande conclusies, waarin het polaire aprotische oplosmiddel dimethylacetamide omvat.
13. Werkwijze volgens één van de conclusies 7-12, waarin het polyoloplosmiddel een glycol omvat, bij voorkeur een alkyleenglycol, gekozen uit ethyleenglycol (1,2- ethaandiol), propyleenglycol (1,3-propaandiol), 1,4-butaandiol en 1,5-pentaandiol.
14. Werkwijze volgens één van de voorgaande conclusies, waarin stap b) wordt uitgevoerd bij een temperatuur van 60 °C tot 100 °C.
15. Werkwijze volgens één van de conclusies 7-14, waarm stap g) wordt uitgevoerd bij een temperatuur van 100 °C tot 190 °C, met meer voorkeur van 120 °C tot 170 °C, met nog meer voorkeur van 130 °C tot 150 °C.
16. Werkwijze volgens één van de voorgaande conclusies, waarin de gewichtsverhouding van polair aprotisch oplosmiddel tot textielafvalmateriaal in het bereik van 1:2 tot 1:40 ligt.
17. Werkwijze volgens één van de voorgaande conclusies, waarin het polyester polyethyleentereftalaat omvat.
18, Werkwijze volgens één van de voorgaande conclusies, waarin het polyurethaan een polyether-polyurea copolymeer omvat, bij voorkeur Elastaan.
19. Werkwijze volgens één van de conclusies 10-18, waarin het acrylpolymeer polyacrylonitril omvat.
20. Werkwijze volgens één van de voorgaande conclusies, waarin het afvalpolymeermateriaal 85-99 gew.% polyester omvat, 1-15 gew.% polyurethaan, en optioneel polyamide en/of acrylpolymeer, waarbij het totaal optelt tot 100 gew.%.
21. Werkwijze volgens één van de voorgaande conclusies, waarin stap b) wordt uitgevoerd gedurende 0,5 tot 8 uur, met meer voorkeur 2 tot 6 uur.
22. Werkwijze volgens één van de conclusies 7-21, waarin stap g) wordt uitgevoerd gedurende 5 tot 60 minuten, met meer voorkeur 10 tot 40 minuten.
23. Werkwijze volgens één van de voorgaande conclusies, verder omvattende de stappen van: i) toevoegen van een reactief oplosmiddel om het polyester herwonnen na stap h) te dispergeren en een dispersie te verkrijgen; j) toevoegen van een depolymerisatiekatalysator aan de dispersie; ky depolymeriseren van het polyester bij condities waaronder monomeren en/of oligomeren opgelost in het reactieve oplosmiddel worden verkregen: waarin het reactieve oplosmiddel een polyol omvat, optioneel het polyol verkregen in stap h).
24. Werkwijze volgens conclusie 23, waarin de depolymerisatie wordt uitgevoerd bij een temperatuur van ten minste 160 °C, bij voorkeur ten minste 180 °C, met meer voorkeur ten minste 190 °C, en met nog meer voorkeur van maximaal 250 °C.
25. Werkwijze volgens conclusie 23 of 24, waarin de katalysator voor het depolymeriseren van het polyester een gefunctionaliseerd magnetisch deeltje omvat dat is gefunctionaliseerd met een katalytische groep.
26. BHET product, verkrijgbaar met een werkwijze volgens één van de conclusies 23-25 en met een totale stikstofinhoud lager dan 1000 ppm, bij voorkeur lager dan 800 ppm, met meer voorkeur lager dan 500 ppm, en met de meeste voorkeur lager dan 300 ppm.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL2035060A NL2035060B1 (en) | 2023-06-09 | 2023-06-09 | A method of recovering polyurethane polymer from a waste polymer textile material that comprises polyester and polyurethane fibers |
| PCT/NL2024/050283 WO2024253517A1 (en) | 2023-06-09 | 2024-06-04 | A method of recovering polyurethane polymer from a waste polymer textile material that comprises polyester and polyurethane fibers |
| TW113121226A TW202506853A (zh) | 2023-06-09 | 2024-06-07 | 自包含聚酯及聚氨酯纖維之廢聚合物紡織材料中回收聚氨酯聚合物之方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL2035060A NL2035060B1 (en) | 2023-06-09 | 2023-06-09 | A method of recovering polyurethane polymer from a waste polymer textile material that comprises polyester and polyurethane fibers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL2035060B1 true NL2035060B1 (en) | 2024-12-19 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL2035060A NL2035060B1 (en) | 2023-06-09 | 2023-06-09 | A method of recovering polyurethane polymer from a waste polymer textile material that comprises polyester and polyurethane fibers |
Country Status (3)
| Country | Link |
|---|---|
| NL (1) | NL2035060B1 (nl) |
| TW (1) | TW202506853A (nl) |
| WO (1) | WO2024253517A1 (nl) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016105200A1 (en) | 2014-12-23 | 2016-06-30 | Ioniqa Technologies B.V. | Polymer degradation |
| CN110790980A (zh) | 2019-10-22 | 2020-02-14 | 宁波大发化纤有限公司 | 一种废聚酯纤维制品中混纺材料的分离除杂方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH513797A (de) * | 1967-12-28 | 1971-10-15 | Teijin Ltd | Verfahren zur Reinigung von rohem bis-(B-Hydroxyäthyl)-terephthalat |
| NL2015749B1 (en) * | 2015-11-09 | 2017-05-26 | Ioniqa Tech B V | PA/PET separation process. |
| KR20210067555A (ko) * | 2019-11-29 | 2021-06-08 | 롯데케미칼 주식회사 | 결정화를 포함하는 폐플라스틱의 화학적 재활용 방법 |
| WO2022115602A1 (en) * | 2020-11-25 | 2022-06-02 | Regenerated Textile Industries Llc | Modular textile recycling system and processes |
| TWI853192B (zh) * | 2021-10-25 | 2024-08-21 | 南亞塑膠工業股份有限公司 | 包含聚酯和彈性纖維的廢舊織物的處理方法 |
-
2023
- 2023-06-09 NL NL2035060A patent/NL2035060B1/en active
-
2024
- 2024-06-04 WO PCT/NL2024/050283 patent/WO2024253517A1/en active Pending
- 2024-06-07 TW TW113121226A patent/TW202506853A/zh unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016105200A1 (en) | 2014-12-23 | 2016-06-30 | Ioniqa Technologies B.V. | Polymer degradation |
| CN110790980A (zh) | 2019-10-22 | 2020-02-14 | 宁波大发化纤有限公司 | 一种废聚酯纤维制品中混纺材料的分离除杂方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2024253517A1 (en) | 2024-12-12 |
| TW202506853A (zh) | 2025-02-16 |
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